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Volumn , Issue 11, 2008, Pages 1687-1689

Diexo-3-aminonorbornane-2-carboxylic acid as highly applicable chiral, source for the enantioselective synthesis of heterocycles

(3) Fülöp, Ferenc a,b Miklós, Ferenc a Forróa, Eniko a

a UNIVERSITY OF SZEGED (Hungary)

b UNIVERSITY OF SZEGED (Hungary)

Author keywords

amino acids; Asymmetric synthesis; Chiral source; Chirality transfer; Domino reactions; Retro reactions; Ring closure

Indexed keywords

3 AMINONORBORNANE 2 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; MICROWAVE RADIATION; SYNTHESIS;

EID: 48249146224 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077793 Document Type: Article

Times cited : (23)

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- 25-4.8 (c 0.51, MeOH).
- 25-4.8 (c 0.51, MeOH).

35
- 48249147300
- Synthesis of Pyrrolo[1,2-a]quinazolines 2 and 3 diexo-3-Aminobicyclo[2.2.1]hept-5-ene-2-carboxamide, )-1, 0.76 g, 5 mmol, levulinic acid or p-toluoylpropionic acid (5.2 mmol, and PTSA (0.05 g) in toluene (25 mL) was refluxed for 14 h. The solvent was then evaporated off, and the residue was dissolved in CHCl3 (10 mL) and the products were separated on a SiO2 column with a mixture of n-hexane-EtOAc-EtOH (5:4:1, Compound, )-2a: yield 86, colorless crystals, mp 173-175 °C (EtOAc-i-Pr2O, α] D25+49 (c 0.27, MeOH, IR (KBr, 3173, 1701, 1659, 707 cm-1. 1H NMR (400 MHz, DMSO, δ, 8.69 (br s, NH, 6.29 (dd, J, 2.7, 5.5 Hz, H-7, 6.17 (dd, J, 2.7, 5.5 Hz, H-8, 4.05 (br s, H-9, 3.34 (d, J, 7.8 Hz, H-8a, 3.27 (br s, H-6, 2.39-2.32 (m, 2 H, H-2, 2.29 (d, J, 7.8 Hz, H-5a, 2.02 (m, H-3, 1.87 m, H-3, 1
- +.

36
- 48249156888
- Syntheses of Pyrrolo[1,2-a]pyrimidines by Microwave-Induced Retro-Diels-Alder Reaction All microwave-induced reactions were performed in sealed reaction vials. Tetracycle 2a, 2b, or 3b (200 mg) was placed in a microwave test tube (10 mL) subsequently sealed with a Teflon cap, which contained a magnetic stirrer and o-DCB (2 mL, The test tube was placed in the microwave (CEM, Discover) cavity. The solutions were irradiated at 250 °C (power 250 W) for 10 min then cooled to r.t, CHCl3 (6 mL) was added, and the solution was transferred to a SiO2 column and eluted with EtOAc. Compound, )-4a: synthesized from, )-2a, colorless crystals, mp 170-172 °C (i-Pr2O-EtOAc, α]D25 -445 (c 0.23, MeOH, ee >99, IR (KBr, 3182, 1734, 1667, 826 cm-1. 1H NMR (400 MHz, DMSO, δ, 8.22 (br s, NH, 7.31 (d, J, 7.8 Hz, H-4, 5.25 dd
- 13C NMR data were identical to the compound (-)-4b.

37
- 48249154916
- R = 16.85 min].
- R = 16.85 min].

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